The X-Men's Wolverine is known for his extremely powerful healing factor and Frank Castle's Punisher certainly put it to the test with one of his most brutal attacks ever. Featured in one of their more classic brawls, the Punisher found himself in the crosshairs of the former Weapon X and he needed to buy some time without Wolverine getting in his way. While his first attack was incredibly gruesome, it only served to tick Logan off. It was the second and third attacks that were truly brutal and horrific, though they did provide Frank Castle with the time he needed to make his escape and get some breathing room in future issues.
Back in the early 2000s, Punisher faced off with Wolverine in Punisher #16-17 from writer Garth Ennis and artist Darick Robertson, providing one of the most insane fights that Wolverine has ever walked away from. It's a well-known Marvel fact that Wolverine is nearly unkillable, having been shot, stabbed, and blown up practically on a daily basis, only surviving thanks to his healing factor. This is why, when Punisher blows off Wolverine's face with a shotgun in Punisher #16, Logan is still standing with his face already starting to heal despite his adamantium skull being on full and gruesome display.
However, it's the subsequent Punisher #17 where things get truly horrific. Knowing that Wolverine will just keep getting back up to hunt him down even after he literally went below the belt and shot off his gonads, Frank Castle resorts to even more drastic measures. Needing the means to give himself a day or two before Logan will inevitably start coming after him again, Castle soon finds the perfect solution, and it's awful: The Punisher uses a steamroller to slowly but completely flatten Logan.
While this absolutely gave Punisher the time and breathing room he was looking for, it did come at the cost of making an enemy out of Wolverine down the line. Wolverine's last act before his healing factor obviously had to go into overdrive was to give Frank the middle claw, and it's evident that the two left their fight on some very bad terms. While Wolverine and Punisher would eventually have a team-up series in 2004, the pair certainly didn't have a lot of kinship or camaraderie (though Castle might have earned Logan's respect).
In any case, getting run over by a steamroller after having his face and tender bits blown off more than proves how powerful Wolverine's mutant ability truly is. While it certainly took time for him to heal and grow everything back, the fact that he was able to walk away as if it never happened will never not be remarkable and serve as one of the coolest mutant powers in the Marvel Universe. Leave it to Punisher to push Wolverine's power to its limit, and it's certainly one of the most horrific and grisly attacks Logan has ever survived.